Cytidine monophosphate

Cytidine monophosphate

Names
IUPAC name [(2R,3S,4R,5R)-5-(4-Amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Other names Cytidylic acid; 5'-Cytidylic acid; Cytidine 5'-monophosphate; Cytidine 5'-phosphate; Cytidylate; 5'-CMP
Identifiers
CAS Number	63-37-6 Y
ChEBI	CHEBI:17361 Y
ChEMBL	ChEMBL307679 Y
ChemSpider	5901 Y
Jmol interactive 3D	Image
PubChem	6131
InChI InChI=1S/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 Y Key: IERHLVCPSMICTF-XVFCMESISA-N Y InChI=1/C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(20-8)3-19-21(16,17)18/h1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6-,7-,8-/m1/s1 Key: IERHLVCPSMICTF-XVFCMESIBY
SMILES c1cn(c(=O)nc1N)[C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(O)O)O)O
Properties
Chemical formula	C9H14N3O8P
Molar mass	323.20 g·mol−1
Acidity (pKa)	0.8, 4.5, 6.3
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Cytidine monophosphate, also known as 5'-cytidylic acid or simply cytidylate, and abbreviated CMP, is a nucleotide that is used as a monomer in RNA.^[1] It is an ester of phosphoric acid with the nucleoside cytidine. CMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase cytosine; hence, a ribonucleoside monophosphate. As a substituent it takes the form of the prefix cytidylyl-.

Metabolism

CMP can be phosphorylated to cytidine diphosphate by the enzyme CMP kinase, with adenosine triphosphate or guanosine triphosphate donating the phosphate group. Since cytidine triphosphate is generated by amination of uridine triphosphate, the main source of CMP is from RNA being decomposed by RNAse.

See also

• Nucleoside
• Oligonucleotide

References